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Stewart

$97+ Cheap flights from Pittsburgh to New Windsor (PIT - SWF)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SWF
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Pittsburgh to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Pittsburgh (PIT) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$229
(Kiwi.com)

One-way from

$97
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$139
From Pittsburgh to New Windsor Stewart
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One-way flight from Pittsburgh to New Windsor Stewart
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Highest demand for flights based on searches. 14% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Pittsburgh to Stewart

Cheapest flights from Pittsburgh to Stewart
Explore the most affordable flight options available from Pittsburgh to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2412:36 pmPIT - SWF
1 stop5h 13mMultiple Airlines
Fri 10/3111:31 amSWF - PIT
1 stop11h 45mMultiple Airlines
Deal found 9/9$229
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/96:51 pmPIT - SWF
1 stop16h 00mMultiple Airlines
Mon 10/1311:01 amSWF - PIT
1 stop12h 15mMultiple Airlines
Deal found 9/9$241
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1712:36 pmPIT - SWF
1 stop5h 13mMultiple Airlines
Mon 10/2011:01 amSWF - PIT
1 stop12h 15mMultiple Airlines
Deal found 9/10$246
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:36 pmPIT - SWF
1 stop5h 13mMultiple Airlines
Mon 11/312:01 pmSWF - PIT
1 stop11h 15mMultiple Airlines
Deal found 9/9$258
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:36 pmPIT - SWF
1 stop5h 13mMultiple Airlines
Sun 11/26:16 pmSWF - PIT
2 stops24h 54mMultiple Airlines
Deal found 9/9$287
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/211:29 amPIT - SWF
1 stop5h 26mMultiple Airlines
Mon 10/611:01 amSWF - PIT
1 stop12h 15mMultiple Airlines
Deal found 9/9$290
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1012:36 pmPIT - SWF
1 stop5h 13mMultiple Airlines
Fri 10/1711:31 amSWF - PIT
1 stop11h 45mMultiple Airlines
Deal found 9/10$302
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2311:29 amPIT - SWF
1 stop5h 26mAllegiant Air
Sun 10/267:11 pmSWF - PIT
1 stop25h 03mAllegiant Air
Deal found 9/11$304
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/88:45 pmPIT - SWF
1 stop21h 36mMultiple Airlines
Mon 10/1311:01 amSWF - PIT
1 stop12h 15mMultiple Airlines
Deal found 9/11$310

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pittsburgh to Stewart that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Pittsburgh to New Windsor that are best for you.

Fly from

Pittsburgh

Fly to

Stewart

Route

Depart

Return

Price

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 10/24

12:36 pm-5:49 pm

1 stop5h 13m

New Windsor Stewart

Fri 10/31

11:31 am-11:16 pm

1 stop11h 45m

$231

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 10/9

6:51 pm-10:51 am

1 stop16h 00m

New Windsor Stewart

Mon 10/13

11:01 am-11:16 pm

1 stop12h 15m

$241

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 10/17

12:36 pm-5:49 pm

1 stop5h 13m

New Windsor Stewart

Mon 10/20

11:01 am-11:16 pm

1 stop12h 15m

$246

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 10/31

12:36 pm-5:49 pm

1 stop5h 13m

New Windsor Stewart

Sun 11/2

6:16 pm-7:10 pm

2 stops24h 54m

$287

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 10/2

11:29 am-4:55 pm

1 stop5h 26m

New Windsor Stewart

Mon 10/6

11:01 am-11:16 pm

1 stop12h 15m

$290

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 10/10

12:36 pm-5:49 pm

1 stop5h 13m

New Windsor Stewart

Fri 10/17

11:31 am-11:16 pm

1 stop11h 45m

$302

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 10/23

11:29 am-4:55 pm

1 stop5h 26m

New Windsor Stewart

Sun 10/26

7:11 pm-8:14 pm

1 stop25h 03m

$304

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Wed 10/8

8:45 pm-6:21 pm

1 stop21h 36m

New Windsor Stewart

Mon 10/13

11:01 am-11:16 pm

1 stop12h 15m

$310

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 10/10

12:36 pm-5:49 pm

1 stop5h 13m

New Windsor Stewart

Mon 10/13

11:01 am-11:16 pm

1 stop12h 15m

$322

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 10/9

11:29 am-4:55 pm

1 stop5h 26m

New Windsor Stewart

Fri 10/10

11:41 am-11:16 pm

1 stop11h 35m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 19 results
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Best time to book a flight from Pittsburgh to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Pittsburgh with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Pittsburgh to New Windsor

What is the cheapest month to book a flight from Pittsburgh to New Windsor?

Currently, October is the cheapest month in which you can book a flight from Pittsburgh to New Windsor (average of $109). Flying from Pittsburgh to New Windsor in December is currently the most expensive (average of $202). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PIT to SWF?

Find hourly flight availability from Pittsburgh to Stewart. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Pittsburgh to New Windsor as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Pittsburgh to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Pittsburgh to Stewart that include hotel bookings?

    Yes. In addition to deals on Pittsburgh to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pittsburgh to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pittsburgh to Stewart.

  • Can I find deals for business class flights from Pittsburgh to Stewart?

    Yes. Cheapflights offers flight deals from Pittsburgh to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Pittsburgh to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Pittsburgh to New Windsor (average of $109). Flying from Pittsburgh to New Windsor in December is currently the most expensive (average of $202). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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